NP-MRD: Showing NP-Card for 11-hydroxychromeno[5,6-c]cinnolin-2-one (NP0152396)

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Record Information

Version

1.0

Created at

2022-09-02 08:51:58 UTC

Updated at

2022-09-02 08:51:58 UTC

NP-MRD ID

NP0152396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxychromeno[5,6-c]cinnolin-2-one

Description

Flavoxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Flavoxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Flavoxanthin has been detected, but not quantified in, several different foods, such as dandelions, apricots, black elderberries, ginkgo nuts, and beverages. This could make flavoxanthin a potential biomarker for the consumption of these foods. 11-hydroxychromeno[5,6-c]cinnolin-2-one is found in Lactarius necator. It was first documented in 2000 (PMID: 11413487). Flavoxanthin is a natural xanthophyll pigment with a golden-yellow color found in small quantities in a variety of plants (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.7500    0.0105    0.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5219    0.1991    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695    1.3863   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    1.5440   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229    0.5472   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553   -0.6056    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478   -1.5865    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781   -1.4776    0.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7675   -2.5046    1.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -0.3275    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -0.0922   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6283   -1.0250    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9743   -0.7748   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3178    0.3922   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3530    1.3165   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122    1.1013   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925    2.0275   -1.1981 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    1.8037   -0.9015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5710    0.6736   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6408   -0.7186    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200    2.1263   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4767    2.4364   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -2.4983    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4675   -3.3325    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -1.9356    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6796   -1.5481   -0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3431    0.6076   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5803    2.2547   -1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
  5 19  1  0
 19 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  8  1  0
 16 11  1  0
 20  6  1  0
 18 19  1  0
  9 24  1  0
  7 23  1  0
  4 22  1  0
  3 21  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
M  END


  Mrv0541 05061310482D          

 20 23  0  0  0  0            999 V2000
    5.0352    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    4.1348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    3.9789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    1.1725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    2.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 11  1  0  0  0  0
 19 13  2  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=CC(=O)O2)C2=C1C1=CC=CC=C1N=N2

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N2O3/c18-11-7-12-9(5-6-13(19)20-12)15-14(11)8-3-1-2-4-10(8)16-17-15/h1-7,18H

> <INCHI_KEY>
WNQBVKOXDIYRFH-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O3

> <MOLECULAR_WEIGHT>
264.2356

> <EXACT_MASS>
264.053492132

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.899147752126808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-6-oxa-17,18-diazatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,8,11,13,15,17-octaen-5-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.0330060796666665

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.020087702093857

> <JCHEM_PKA_STRONGEST_BASIC>
1.2775672275348264

> <JCHEM_POLAR_SURFACE_AREA>
72.31

> <JCHEM_REFRACTIVITY>
73.3923

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-6-oxa-17,18-diazatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,8,11,13,15,17-octaen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.399   4.226   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   5.681   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.887   3.935   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.895   6.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.838   6.845   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.326   6.554   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.350   3.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   5.099   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.846   5.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   6.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.862   3.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.342   4.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.179   5.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.366   4.808   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.358   5.972   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.374   7.718   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.862   7.427   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.870   2.189   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.691   4.808   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.830   3.935   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5   13                                                       
CONECT    7   11   12                                                       
CONECT    8    3   10   14                                                  
CONECT    9    5   12   15                                                  
CONECT   10    4    8   16                                                  
CONECT   11    7   14   18                                                  
CONECT   12    7    9   20                                                  
CONECT   13    6   19   20                                                  
CONECT   14    8   11   15                                                  
CONECT   15    9   14   17                                                  
CONECT   16   10   17                                                       
CONECT   17   15   16                                                       
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxy-2H-benzo(c)pyrano(2,3-H)cinnolin-2-one	HMDB
11-Hydroxy-2H-benzo[c]pyrano[2,3-H]cinnolin-2-one, 9ci	HMDB
Necatorin	HMDB

Chemical Formula

C₁₅H₈N₂O₃

Average Mass

264.2356 Da

Monoisotopic Mass

264.05349 Da

IUPAC Name

9-hydroxy-6-oxa-17,18-diazatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,8,11,13,15,17-octaen-5-one

Traditional Name

9-hydroxy-6-oxa-17,18-diazatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,8,11,13,15,17-octaen-5-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=CC(=O)O2)C2=C1C1=CC=CC=C1N=N2

InChI Identifier

InChI=1S/C15H8N2O3/c18-11-7-12-9(5-6-13(19)20-12)15-14(11)8-3-1-2-4-10(8)16-17-15/h1-7,18H

InChI Key

WNQBVKOXDIYRFH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lactarius necator	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Benzofuran
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	2.03	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.02	ChemAxon
pKa (Strongest Basic)	1.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.39 m³·mol⁻¹	ChemAxon
Polarizability	25.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036868

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015822

KNApSAcK ID

C00003772

Chemspider ID

Not Available

KEGG Compound ID

C08594

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flavoxanthin

METLIN ID

Not Available

PubChem Compound

131752071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for 11-hydroxychromeno[5,6-c]cinnolin-2-one (NP0152396)

MOL for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

3D MOL for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

3D SDF for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

3D-SDF for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

PDB for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

3D PDB for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

SMILES for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

INCHI for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

Structure for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)

3D Structure for NP0152396 (11-hydroxychromeno[5,6-c]cinnolin-2-one)